Amine compounds, their preparation processes and the organic electroluminescent devices using the same

Abstract

The claimed invention relates to compounds of the formula (I): wherein X, Y, Ar 1 , Ar 2 , Ar 3 and Ar 4 are as defined in the specification. The claimed invention also relates to the preparation processes of the said compounds and their uses in the organic electroluminescent device.

1. A compound of the formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         X and Y are identical or different, and independently represent straight or branched C 1-6  alkyl, or C 3-8  aryl, 
         Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted C 3-8  aryl groups. 
       
     
     
       2. The compound according to  claim 1 , wherein X and Y are identical or different, and independently represent methyl or ethyl. 
     
     
       3. The compound according to  claim 1 , wherein X and Y together with C atom to which they are attached may form a benzocyclopentane ring. 
     
     
       4. The compound according to  claim 1 , wherein X and Y together with C atom to which they are attached may form a fluorene. 
     
     
       5. The compound according to  claim 1 , wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted phenyl. 
     
     
       6. The compound according to  claim 5 , wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent phenyl or tolyl. 
     
     
       7. The compound according to  claim 1  having the structural formula (II) 
       
         
           
           
               
               
           
         
         wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted C 3-20  aryl groups. 
       
     
     
       8. The compound according to  claim 1  having the structural formula (III) 
       
         
           
           
               
               
           
         
         wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted C 3-20  aryl groups. 
       
     
     
       9. The compound according to  claim 1  having the structural formula (IV) 
       
         
           
           
               
               
           
         
         wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted C 3-20  aryl groups. 
       
     
     
       10. The compound according to  claim 1  having the structural formula (V) 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are identical or different, and represent C 1-6 alkyl; and Ar 1 , Ar 2 , Ar 3  and Ar 4  are identical or different, and represent optionally substituted C 3-20  aryl groups. 
       
     
     
       11. The compound according to any one of  claims 7  to  10 , which is selected from the following compounds: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       12. The compound according to  claim 1 , which is used in an organic electroluminescent device. 
     
     
       13. The compound according to  claim 12 , which is used in the hole-injection layer of an organic electroluminescent device. 
     
     
       14. A process for preparing the compounds according to any one of  claims 1  to  13  comprising the following steps:
 adding suitable amounts of the compounds having the structural formulas (A) and (B), nitrobenzene and potassium carbonate into a proper container, 
 
       
         
           
           
               
               
           
         
         wherein 
         Ra and Rb are identical or different, and are independently selected from the group consisting of hydrogen, straight or branched alkyl, alkenyl or alkynyl, cycloalkyl, alkoxy, halo, amino, nitro, cyano, hydroxy, heterocyclyl, aryl and heteroaryl,
 or Ra and Rb together with C atom to which they are attached form an optionally substituted saturated or unsaturated cyclohydrocarbon, heterocyclic ring, aryl ring, heteroaryl ring, benzene ring-fused cyclic hydrocarbon, fused benzene ring-fused cyclic hydrocarbon, benzoheterocyclic ring, fused benzene rings-fused heterocyclic ring or polyheterocyclic ring; and 
 
         Rc and Rd are identical or different, and are independently selected from the group consisting of hydrogen, straight or branched alkyl, alkenyl or alkynyl, cycloalkyl, alkoxy, halo, amino, nitro, cyano, hydroxy, heterocyclyl, aryl and heteroaryl; or
 Rc and Rd together with C atom to which they are attached form an optionally substituted saturated or unsaturated cyclohydrocarbon, heterocyclic ring, aryl ring, heteroaryl ring, benzene ring-fused cyclic hydrocarbon, fused benzene ring-fused cyclic hydrocarbon, benzoheterocyclic ring, fused benzene rings-fused heterocyclic ring or polyheterocyclic ring; 
 adding a suitable amount of copper powder under inert gas; 
 
         heating the mixture with stirring; and 
         adding an amount of 1-bromonaphthalene to react. 
       
     
     
       15. An organic electroluminescent device, which comprises the compound according to any one of  claims 1  or  2 - 13 . 
     
     
       16. The organic electroluminescent device according to  claim 15 , wherein the said organic electroluminescent device is a display. 
     
     
       17. The organic electroluminescent device according to  claim 15 , wherein the said compound is used as the material for the hole-injection layer.